CA2394809A1 - Benzazole derivatives and their use as jnk modulators - Google Patents
Benzazole derivatives and their use as jnk modulators Download PDFInfo
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Abstract
The present invention is related to benzazole derivatives accord-ing to formula (I) wherein X is O, S, or NR O with R0 being H or an unsubstituted or substituted C1-C6alkyl, and G is an unsubstituted or substituted pyrimidinyl group, notably for use as pharmaceutically active compounds, as well as to phar-maceutical formulations containing such benzazoles derivatives. Said benzazoles derivatives are efficient modulators of the JNK pathway, they are in particular ef-ficient and selective inhibitors of JNK2 and/or 3.
Claims (30)
1. Benzazole derivatives according to formula I
as well as its tautomers, its geometrical isomers, its optically active forms as enantio-mers, diastereomers and its racemate forms, as well as pharmaceutically acceptable salts thereof, wherein X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1-C6 alkyl;
G is an unsubstituted or substituted pyrimidinyl group;
R1 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-thioalkoxy, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, unsubstituted or substituted C1-C6 alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, sulfonamide, unsubstituted or substituted hydrazides;
R2 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, unsubstituted or substituted C1-C6-alkyl-aryl, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted C1-C6-alkyl-heteroaryl, -C(O)-OR3, -C(O)-R3, -C(O)-NR3R3', -(SO2)R3, with R3 and R3' being independently selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C2-C6 alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted C1-C6-alkyl aryl, unsubstituted or substituted C1-C6-alkyl heteroaryl;
with the proviso that if X is S, R1 and R2 are H, G may be neither of the following pyrimidines with the further proviso that if X is NH, R1 and R2 are H, G may be neither of the following pyrimidines:
with the final proviso that if X is N-CH3, R1 and R2 are H, G may be neither of the following pyrimidines
as well as its tautomers, its geometrical isomers, its optically active forms as enantio-mers, diastereomers and its racemate forms, as well as pharmaceutically acceptable salts thereof, wherein X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1-C6 alkyl;
G is an unsubstituted or substituted pyrimidinyl group;
R1 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-thioalkoxy, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, unsubstituted or substituted C1-C6 alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, sulfonamide, unsubstituted or substituted hydrazides;
R2 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, unsubstituted or substituted C1-C6-alkyl-aryl, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted C1-C6-alkyl-heteroaryl, -C(O)-OR3, -C(O)-R3, -C(O)-NR3R3', -(SO2)R3, with R3 and R3' being independently selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C2-C6 alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted C1-C6-alkyl aryl, unsubstituted or substituted C1-C6-alkyl heteroaryl;
with the proviso that if X is S, R1 and R2 are H, G may be neither of the following pyrimidines with the further proviso that if X is NH, R1 and R2 are H, G may be neither of the following pyrimidines:
with the final proviso that if X is N-CH3, R1 and R2 are H, G may be neither of the following pyrimidines
2. Benzazole derivatives according to formula I
as well as its tautomers, its geometrical isomers, its optically active forms as enantiomers, diastereomers and its racemate forms, as well as pharmaceutically acceptable salts thereof, wherein X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1-C6 alkyl;
G is an unsubstituted or substituted pyrimidinyl group;
R1 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-thioalkoxy, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, unsubstituted or substituted C1-C6 alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, vitro, sulfoxy, sulfonyl, sulfonamide, unsubstituted or substituted hydrazides;
R2 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, unsubstituted or substituted C1-C6-alkyl-aryl, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted C1-C6-alkyl-heteroaryl, -C(O)-OR3, -C(O)-R3, -C(O)-NR3R3', -(SO2)R3, with R3 and R3' being independently selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C2-C6 alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted C1-C6-alkyl aryl, unsubstituted or substituted C1-C6-alkyl heteroaryl, for use as a medicament.
as well as its tautomers, its geometrical isomers, its optically active forms as enantiomers, diastereomers and its racemate forms, as well as pharmaceutically acceptable salts thereof, wherein X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1-C6 alkyl;
G is an unsubstituted or substituted pyrimidinyl group;
R1 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-thioalkoxy, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, unsubstituted or substituted C1-C6 alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, vitro, sulfoxy, sulfonyl, sulfonamide, unsubstituted or substituted hydrazides;
R2 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, unsubstituted or substituted C1-C6-alkyl-aryl, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted C1-C6-alkyl-heteroaryl, -C(O)-OR3, -C(O)-R3, -C(O)-NR3R3', -(SO2)R3, with R3 and R3' being independently selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C2-C6 alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted C1-C6-alkyl aryl, unsubstituted or substituted C1-C6-alkyl heteroaryl, for use as a medicament.
3. Benzothiazole derivatives of formula I, as well as their tautomers according to formula II, according to claim 1 or 2 their geometrical isomers, their optically active forms as enantiomers, diastereomers and their racemate fortes, as well as pharmaceutically acceptable salts thereof, wherein G is an unsubstituted or substituted pyrimidinyl group;
R1 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-thioalkoxy, unsubstit-uted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsub-stituted or substituted C2-C6-alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, unsubstituted or substituted C1-C6 alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, sulfonamide, unsubstituted or substituted hydrazides;
with the proviso that if R1 is H, G may be neither of the following pyrimidines
R1 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-thioalkoxy, unsubstit-uted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsub-stituted or substituted C2-C6-alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, unsubstituted or substituted C1-C6 alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, sulfonamide, unsubstituted or substituted hydrazides;
with the proviso that if R1 is H, G may be neither of the following pyrimidines
4. A benzazole derivative according to claim 1 or 2, wherein R2 is hydrogen, an unsubstituted or substituted C1-C6 alkyl, an unsubstituted or substituted C1-C6 alkylaryl or C1-C6 alkyl-heteroaryl group, -C(O)-R3, -C(O)-NR3R3', -(SO2)R3, whereby R3 and R3' are as above defined.
5. A benzazole derivative according to claim 4, wherein R2 is hydrogen and R1, X and G
are as above defined.
are as above defined.
6. A benzazole derivative according to any of the preceding claims, wherein R1 is selected from the group consisting of hydrogen, halogen, C1-C6 alkyl or C1-C6 alkoxy.
7. A benzazole derivative according to claim 4, wherein R3 and R3' are selected from the group consisting of hydrogen, C1-C6 alkyl, aryl, heteroaryl, C1-C6-alkyl aryl, alkyl heteroaryl.
8. A benzazole derivative according to claim 7, wherein R3 and R3' is hydrogen or C1-C6 alkyl.
9 A benzazole derivative according any of the preceding claims, wherein said aryl or heteroaryl group is substituted with at least one substituent selected from the group consisting of unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C1-C6 alkoxy, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted alkynyl, amino, aminoacyl, aminocarbonyl, unsubstituted or substituted Cl-C6-alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, C1-C6 thioalkoxy.
10. A benzazole derivative according to any of claims 1 to 9, wherein G is a pyrimidinyl group wherein L is selected from the group comprising or consisting of hydrogen, unsub-stituted or substituted C1-C6 alkyl, unsubstituted or substituted C1-C6 alkoxy, unsub-stituted or substituted C1-C6 thioalkoxy, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C2-C6 alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, amino-(C1-C10)alkyl, amino- unsubstituted or substituted (C1-C10)-alkyl-aryl, amino- unsubstituted or substituted (C1-C10)alkyl-heteroaryl, unsubstituted or substituted C1-C6 alkoxycarbonyl, carboxyl, cyano, halogen, hydroxy, vitro, sulfoxy, sulfonyl, unsubstituted or substituted aryl, unsub-stituted or substituted heteroaryl, unsubstituted or substituted 3-8 membered cycloalkyl, optionally containing at least one heteroatom selected from N, O, S, and unsubstituted or substituted hydrazido groups.
11. A benzazole derivative according to claim 10, wherein L is a group -N(R a, R b) or -OR a, with R a and R b being each independently selected from the group consisting of H, unsubstituted or substituted (C1-C10)-alkyl, unsubstituted or substituted C1-C6 alkyl-aryl, unsubstituted or substituted C1-C6-alkyl-heteroaryl, unsubstituted or substituted aryl or heteroaryl and unsubstituted or substituted 4-8 membered saturated or unsaturated cycloalkyl.
12. A benzazole derivative according to claim 11 wherein L is selected from wherein n is 1 to 10, preferably 1 to 6, R5 and R5' are independently selected from each other from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted aryl or hetero-aryl, substituted or unsubstituted C1-C6 alkyl-aryl and substituted or unsubstituted C1-C6-alkyl-heteroaryl.
13. A benzazole derivative according to claim 12, wherein X is S, R1 is H and R2 is H.
14. A benzazole derivative according to any of the preceding claims, wherein X
is S, R1 and R2 are H or C1-C6 alkyl, G is a pyrimidinyl group with L being either wherein n is 0, 1 or 2 and R5 is an aryl or heteroaryl.
is S, R1 and R2 are H or C1-C6 alkyl, G is a pyrimidinyl group with L being either wherein n is 0, 1 or 2 and R5 is an aryl or heteroaryl.
15. A benzazole derivative according to claim 14, wherein R5 is phenyl, pyridyl, imidazolyl.
16. A benzazole derivative according to any of the preceding claims selected from the following group:
1,3-benzothiazol-2-yl(2-chloro-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl(2,6-dimethoxy-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl(2-chloro-6-methyl-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl [2-(methylsulfanyl)-4-pyrimidinyl] acetonitrile 1,3-benzothiazol-2-yl {6-chloro-5-nitro-4-pyrimidinyl}acetonitrile 1,3-benzothiazol-2-yl(hydroxy-4--4- pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl(2-phenyl-4-quinazolinyl)acetonitrile (2-chloropyrimidin-4-yl)[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]acetonitrile (2E)-(2-chloro-4-pyrimidinyl)(3-methyl-1,3-benzothiazol-2(3H)-ylidene)ethanenitrile 1,3-benzothiazol-2-yl(2-{[2-(1H-imidazol-5-yl)ethyl]amino)-4-pyrimidinyl)-acetonitrile 1, 3-benzothiazol-2-yl[2-(1-pip erazinyl)-4-pyrimidinyl] acetonitrile 1,3-benzothiazol-2-yl[2-(4-benzyl-1-piperidinyl)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl[2-(4-methyl-1-piperazinyl)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl[2-(4-morpholinyl)-4-pyrimidinyl]acetonitri1e 1,3-benzothiazol-2-yl[2-(methylamino)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl(2-{4-[2-(4-morpholinyl)ethyl]-1-piperazinyl)-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl{2-[4-(benzyloxy)-1-piperidinyl]-4-pyrimidinyl}
acetonitrile 1,3-benzothiazol-2-yl[2-(4-hydroxy-1-piperidinyl)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl(2-hydrazino-4-pyrimidinyl)acetonitrile 1, 3-benzothiazol-2-yl(2-{[2-(dimethylamino)ethyl]amino]-4-pyrimidinyl) acetonitrile 1,3-benzothiazol-2-yl[2-(dimethylamino)-4-pyrimidinyl]acetonitri1e 1,3-benzothiazol-2-yl{2-[(2-methoxyethyl)amino]-4-pyrimidinyl} acetonitrile 1,3-benzothiazol-2-yl{2-[(2-hydroxyethyl)amino]-4-pyrimidinyl} acetonitrile 1,3-benzothiazol-2-yl[2-(propylamino)-4-pyrimidinyl]acetonitrile 1, 3-benzothiazol-2-yl(2-{[3-(1H-imidazo1-1-yl)propyl]amino}-4-pyrimidinyl)acetonitrile 1,3-b enzothiazol-2-yl[2-(1-pyrrolidinyl)-4-pyrimidinyl] acetonitrile 1,3-benzothiazol-2-yl {2-[(2-phenylethyl)amino]-4-pyrimidinyl} acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(2-pyridinyl)ethyl]amino}-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl {2-[(2-pyridinylmethyl)amino]-4-pyrimidinyl]
acetonitrile 1,3-benzothiazol-2-yl {2-[4-(1H-1,2,3-benzotriazol-1-yl)-1-piperidinyl]-4-pyrimidinyl) acetonitrile 1,3-benzothiazol-2-yl{2-[4-(2-pyrazinyl)-1-piperazinyl]-4-pyrimidinyl~
acetonitrile 1,3-benzothiazol-2-yl{2-[4-(2-pyrimidinyl)-1-piperazinyl]-4-pyrimidinyl}
acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3-pyridinyl)ethyl]amino}-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl(5-bromo-2-{[2-(dimethylamino)ethyl]amino}-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl{2-[(2-morpholin-4-ylethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl[2-(4-{3-[(trifluoromethyl)sulfonyl]anilino}piperidin-1-yl)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl(2-{[3-(2-oxopyrrolidin-1-yl)propyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{methyl[3-(methylamino)propyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[3-(4-methylpiperazin-1-yl)propyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl{2-[(3-morpholin-4-ylpropyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(1-methyl-1H-imidazol-4-yl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1, 3-b enzothiazol-2-yl(2-{[2-(1H-indol-3-yl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-hydroxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile tert-butyl({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)acetate {2-[(3-aminopropyl)amino]pyrimidin-4-yl}(1, 3-benzothiazol-2-yl)acetonitrile {2-[(2-aminoethyl)amino]pyrimidin-4-yl}(1,3-benzothiazol-2-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[3-(dimethylamino)propyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl {2-[(2-piperidin-1-ylethyl)amino]pyrimidin-4-yl}
acetonitrile 1, 3-benzothiazol-2-yl(2-{[2-(1-methyl-1 H-imidazol-5-yl)ethyl]amino}pyrimidin-yl)acetonitrile 1,3-benzothiazol-2-yl[2-(benzylamino)pyrimidin-4-yl]acetonitrile isopropyl3-({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)propanoate 1,3-benzothiazol-2-yl {2-[(3-hydroxypropyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yI{2-[(pyridin-3-ylmethyl)amino]pyrimidin-4-yl}
acetonitrile (2-aminopyrimidin-4-yl)(1,3-benzothiazol-2-yl)acetonitrile 1,3-benzothiazol-2-yl{2-[(pyridin-4-ylmethyl)amino]pyrimidin-4-yl}acetonitrile tent-butyl4-[2-({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)ethyl]phenylcarbamate (2-{[2-(4-aminophenyl)ethyl]amino}pyrimidin-4-yl)(1,3-benzothiazol-2-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3,4-dimethoxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3-methoxyphenyl)ethyl]amino pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(2-fluorophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl[2-({2-[3-(trifluoromethyl)phenyl]ethyl}amino)pyrimidin-4-yl] acetonitrile 1,3-benzothiazol-2-yl{2-[(2-hydroxy-2-phenylethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl{2-[(2-{[3-(trifluoromethyl)pyridin-2-yl] amino}ethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3-chlorophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3,4-dichlorophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2,-{[2-(4-methoxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-methylphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1, 3-benzothia zol-2-yl(2-{[2-(3-fluorophenyl)ethyl]amino}pyrimidin-4-yl) acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-phenoxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(2-phenoxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-bromophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-fluorophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl {2-[(2-[ 1,1'-biphenyl]-4-ylethyl)amino]pyrimidin-4-yl} acetonitrile 1,3-benzothiazol-2-yl{2-[(2-{4-[hydroxy(oxido)amino]phenyl}ethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(1H-1,2,4-triazol-1-yl)ethyl]amino]pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[3-(1H-pyrazol-1-yl)propyl]amino)pyrimidin-4-yl)acetonitrile 4-[2-({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)ethyl]benzenesulfonamide {2-[(2-pyridin-3-ylethyl)amino]pyrimidin-4-yl}[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(1H-tetraazol-5-ylmethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl[2-(benzyloxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(4-pyridin-3-ylbenzyl)oxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl[2-(pyridin-4-ylmethoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(pyridin-2-ylmethoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(3-pyridin-2-ylpropoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(4-methoxybenzyl)oxy]pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(pyridin-3-ylmethoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[2-(4-methoxyphenyl)ethoxy]pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-([1,1'-biphenyl]-3-ylmethoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(3,4,5-trimethoxybenzyl)oxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl{2-[(3,4-dichlorobenzyl)oxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl[2-({3-[(dimethylamino)methyl]benzyl}oxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(1-oxidopyridin-3-yl)methoxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[4-(morpholin-4-ylmethyl)benzyl]oxy}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl{2-[(4-pyridin-2-ylbenzyl)oxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[4-(piperidin-1-ylmethyl)benzyl]oxy]pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl[2-(4-methoxyphenoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(4-butoxyphenoxy)pyrimidin-4-yl]acetonitrile {2-[4-(4-acetylpiperazin-1-yl)phenoxy]pyrimidin-4-yl}(1,3-benzothiazol-2-yl)acetonitrile [2-(4-methoxyphenoxy)pyrimidin-4-yl][5-(trifluoromethyl)-1,3-benzothiazol-2-yl]acetonitrile 1,3-benzothiazol-2-yl(pyrimidin-4-yl)acetonitrile N-[2-({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)ethyl]-4-chlorobenzamide 1,3-benzothiazol-2-yl(2-methoxy-4-pyrimidinyl)acetonitrile
1,3-benzothiazol-2-yl(2-chloro-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl(2,6-dimethoxy-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl(2-chloro-6-methyl-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl [2-(methylsulfanyl)-4-pyrimidinyl] acetonitrile 1,3-benzothiazol-2-yl {6-chloro-5-nitro-4-pyrimidinyl}acetonitrile 1,3-benzothiazol-2-yl(hydroxy-4--4- pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl(2-phenyl-4-quinazolinyl)acetonitrile (2-chloropyrimidin-4-yl)[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]acetonitrile (2E)-(2-chloro-4-pyrimidinyl)(3-methyl-1,3-benzothiazol-2(3H)-ylidene)ethanenitrile 1,3-benzothiazol-2-yl(2-{[2-(1H-imidazol-5-yl)ethyl]amino)-4-pyrimidinyl)-acetonitrile 1, 3-benzothiazol-2-yl[2-(1-pip erazinyl)-4-pyrimidinyl] acetonitrile 1,3-benzothiazol-2-yl[2-(4-benzyl-1-piperidinyl)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl[2-(4-methyl-1-piperazinyl)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl[2-(4-morpholinyl)-4-pyrimidinyl]acetonitri1e 1,3-benzothiazol-2-yl[2-(methylamino)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl(2-{4-[2-(4-morpholinyl)ethyl]-1-piperazinyl)-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl{2-[4-(benzyloxy)-1-piperidinyl]-4-pyrimidinyl}
acetonitrile 1,3-benzothiazol-2-yl[2-(4-hydroxy-1-piperidinyl)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl(2-hydrazino-4-pyrimidinyl)acetonitrile 1, 3-benzothiazol-2-yl(2-{[2-(dimethylamino)ethyl]amino]-4-pyrimidinyl) acetonitrile 1,3-benzothiazol-2-yl[2-(dimethylamino)-4-pyrimidinyl]acetonitri1e 1,3-benzothiazol-2-yl{2-[(2-methoxyethyl)amino]-4-pyrimidinyl} acetonitrile 1,3-benzothiazol-2-yl{2-[(2-hydroxyethyl)amino]-4-pyrimidinyl} acetonitrile 1,3-benzothiazol-2-yl[2-(propylamino)-4-pyrimidinyl]acetonitrile 1, 3-benzothiazol-2-yl(2-{[3-(1H-imidazo1-1-yl)propyl]amino}-4-pyrimidinyl)acetonitrile 1,3-b enzothiazol-2-yl[2-(1-pyrrolidinyl)-4-pyrimidinyl] acetonitrile 1,3-benzothiazol-2-yl {2-[(2-phenylethyl)amino]-4-pyrimidinyl} acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(2-pyridinyl)ethyl]amino}-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl {2-[(2-pyridinylmethyl)amino]-4-pyrimidinyl]
acetonitrile 1,3-benzothiazol-2-yl {2-[4-(1H-1,2,3-benzotriazol-1-yl)-1-piperidinyl]-4-pyrimidinyl) acetonitrile 1,3-benzothiazol-2-yl{2-[4-(2-pyrazinyl)-1-piperazinyl]-4-pyrimidinyl~
acetonitrile 1,3-benzothiazol-2-yl{2-[4-(2-pyrimidinyl)-1-piperazinyl]-4-pyrimidinyl}
acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3-pyridinyl)ethyl]amino}-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl(5-bromo-2-{[2-(dimethylamino)ethyl]amino}-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl{2-[(2-morpholin-4-ylethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl[2-(4-{3-[(trifluoromethyl)sulfonyl]anilino}piperidin-1-yl)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl(2-{[3-(2-oxopyrrolidin-1-yl)propyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{methyl[3-(methylamino)propyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[3-(4-methylpiperazin-1-yl)propyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl{2-[(3-morpholin-4-ylpropyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(1-methyl-1H-imidazol-4-yl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1, 3-b enzothiazol-2-yl(2-{[2-(1H-indol-3-yl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-hydroxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile tert-butyl({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)acetate {2-[(3-aminopropyl)amino]pyrimidin-4-yl}(1, 3-benzothiazol-2-yl)acetonitrile {2-[(2-aminoethyl)amino]pyrimidin-4-yl}(1,3-benzothiazol-2-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[3-(dimethylamino)propyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl {2-[(2-piperidin-1-ylethyl)amino]pyrimidin-4-yl}
acetonitrile 1, 3-benzothiazol-2-yl(2-{[2-(1-methyl-1 H-imidazol-5-yl)ethyl]amino}pyrimidin-yl)acetonitrile 1,3-benzothiazol-2-yl[2-(benzylamino)pyrimidin-4-yl]acetonitrile isopropyl3-({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)propanoate 1,3-benzothiazol-2-yl {2-[(3-hydroxypropyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yI{2-[(pyridin-3-ylmethyl)amino]pyrimidin-4-yl}
acetonitrile (2-aminopyrimidin-4-yl)(1,3-benzothiazol-2-yl)acetonitrile 1,3-benzothiazol-2-yl{2-[(pyridin-4-ylmethyl)amino]pyrimidin-4-yl}acetonitrile tent-butyl4-[2-({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)ethyl]phenylcarbamate (2-{[2-(4-aminophenyl)ethyl]amino}pyrimidin-4-yl)(1,3-benzothiazol-2-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3,4-dimethoxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3-methoxyphenyl)ethyl]amino pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(2-fluorophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl[2-({2-[3-(trifluoromethyl)phenyl]ethyl}amino)pyrimidin-4-yl] acetonitrile 1,3-benzothiazol-2-yl{2-[(2-hydroxy-2-phenylethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl{2-[(2-{[3-(trifluoromethyl)pyridin-2-yl] amino}ethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3-chlorophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(3,4-dichlorophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2,-{[2-(4-methoxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-methylphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1, 3-benzothia zol-2-yl(2-{[2-(3-fluorophenyl)ethyl]amino}pyrimidin-4-yl) acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-phenoxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(2-phenoxyphenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-bromophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(4-fluorophenyl)ethyl]amino}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl {2-[(2-[ 1,1'-biphenyl]-4-ylethyl)amino]pyrimidin-4-yl} acetonitrile 1,3-benzothiazol-2-yl{2-[(2-{4-[hydroxy(oxido)amino]phenyl}ethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(1H-1,2,4-triazol-1-yl)ethyl]amino]pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl(2-{[3-(1H-pyrazol-1-yl)propyl]amino)pyrimidin-4-yl)acetonitrile 4-[2-({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)ethyl]benzenesulfonamide {2-[(2-pyridin-3-ylethyl)amino]pyrimidin-4-yl}[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(1H-tetraazol-5-ylmethyl)amino]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl[2-(benzyloxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(4-pyridin-3-ylbenzyl)oxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl[2-(pyridin-4-ylmethoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(pyridin-2-ylmethoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(3-pyridin-2-ylpropoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(4-methoxybenzyl)oxy]pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(pyridin-3-ylmethoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[2-(4-methoxyphenyl)ethoxy]pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-([1,1'-biphenyl]-3-ylmethoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(3,4,5-trimethoxybenzyl)oxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl{2-[(3,4-dichlorobenzyl)oxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl[2-({3-[(dimethylamino)methyl]benzyl}oxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl{2-[(1-oxidopyridin-3-yl)methoxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[4-(morpholin-4-ylmethyl)benzyl]oxy}pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl{2-[(4-pyridin-2-ylbenzyl)oxy]pyrimidin-4-yl}acetonitrile 1,3-benzothiazol-2-yl(2-{[4-(piperidin-1-ylmethyl)benzyl]oxy]pyrimidin-4-yl)acetonitrile 1,3-benzothiazol-2-yl[2-(4-methoxyphenoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(4-butoxyphenoxy)pyrimidin-4-yl]acetonitrile {2-[4-(4-acetylpiperazin-1-yl)phenoxy]pyrimidin-4-yl}(1,3-benzothiazol-2-yl)acetonitrile [2-(4-methoxyphenoxy)pyrimidin-4-yl][5-(trifluoromethyl)-1,3-benzothiazol-2-yl]acetonitrile 1,3-benzothiazol-2-yl(pyrimidin-4-yl)acetonitrile N-[2-({4-[1,3-benzothiazol-2-yl(cyano)methyl]pyrimidin-2-yl}amino)ethyl]-4-chlorobenzamide 1,3-benzothiazol-2-yl(2-methoxy-4-pyrimidinyl)acetonitrile
17. Benzazole derivatives according to claim 16, selected from the group consisting of 1,3-benzothiazol-2-yl(2-chloro-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl[2-(methylsulfanyl)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl(2-{[2-(1H-imidazol-5-yl)ethyl]amino}-4-pyrimidinyl)acetonitrile 1,3-benzothiazol-2-yl[2-(methylamino)-4-pyrimidinyl]acetonitrile 1,3-benzothiazol-2-yl{2-[(2-hydroxyethyl)amino]-4-pyrimidinyl}acetonitrile 1,3-benzothiazol-2-yl[2-(benzyloxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl[2-(4-methoxyphenoxy)pyrimidin-4-yl]acetonitrile 1,3-benzothiazol-2-yl(2-methoxy-4-pyrimidinyl)acetonitrile I,3-benzothiazol-2-yl(2-{[2-(3-pyridinyl)ethyl]amino}-4-pyrimidinyl)acetonitrile.
18. Use of a benzazole derivatives according to formula I
as well as its tautomers, its geometrical isomers, its optically active forms as enantio-mers, diastereomers and its racemate forms, as well as pharmaceutically acceptable salts thereof, wherein X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1-C6 alkyl;
G is an unsubstituted or substituted pyrimidinyl group;
R1 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-thioalkoxy, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, unsubstituted or substituted C1-C6 alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, sulfonamide, unsubstituted or substituted hydrazides;
R2 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, unsubstituted or substituted C1-C6-alkyl-aryl, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted C1-C6-alkyl-heteroaryl, -C(O)-OR3, -C(O)-R3, -C(O)-NR3R3', -(SO2)R3, with R3 and R3' being independently selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C2-C6 alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted C1-C6-alkyl aryl, unsubstituted or substituted C1-C6-alkyl heteroaryl, for the preparation of a pharmaceutical composition for the modulation of the JNK
pathway.
as well as its tautomers, its geometrical isomers, its optically active forms as enantio-mers, diastereomers and its racemate forms, as well as pharmaceutically acceptable salts thereof, wherein X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1-C6 alkyl;
G is an unsubstituted or substituted pyrimidinyl group;
R1 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkoxy, unsubstituted or substituted C1-C6-thioalkoxy, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, primary, secondary or tertiary amino groups, aminoacyl, aminocarbonyl, unsubstituted or substituted C1-C6 alkoxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, carboxyl, cyano, halogen, hydroxy, nitro, sulfoxy, sulfonyl, sulfonamide, unsubstituted or substituted hydrazides;
R2 is selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6-alkyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, unsubstituted or substituted C1-C6-alkyl-aryl, unsubstituted or substituted aryl or heteroaryl, unsubstituted or substituted C1-C6-alkyl-heteroaryl, -C(O)-OR3, -C(O)-R3, -C(O)-NR3R3', -(SO2)R3, with R3 and R3' being independently selected from the group comprising or consisting of hydrogen, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C2-C6 alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted C1-C6-alkyl aryl, unsubstituted or substituted C1-C6-alkyl heteroaryl, for the preparation of a pharmaceutical composition for the modulation of the JNK
pathway.
19. Use according to claim 18 for the treatment or prevention of disorders associated with the abnormal expression or activity of JNK.
20. Use according to claim 18 for the treatment or prevention of disorders associated with the abnormal expression or activity of JNK2 and/or 3.
21. Use of a benzazole derivative according to any of claims 1 to 17 for the preparation of a pharmaceutical composition for the treatment of neuronal disorders including epi-lepsy, Alzheimer's disease, Huntington's disease, Parkinson's disease, retinal diseases, spinal cord injury, head trauma.
22. Use of a benzazole derivative according to any of claims 1 to 17 for the preparation of a pharmaceutical composition for the treatment of autoimmune diseases including Multiple Sclerosis, inflammatory bowel disease (IBD), rheumatoid arthritis, asthma, septic schock, transplant rejection.
23. Use of a benzazole derivative according to any of claims 1 to 17 for the preparation of a pharmaceutical composition for the treatment of cancer including breast-, colorectal, pancreatic cancer.
24. Use of a benzazole derivative according to any of claims 1 to 17 for the preparation of a pharmaceutical composition for the treatment of cardiovascular diseases including stroke, arterosclerosis, myocordial infarction, myocordial reperfusion injury.
25. Use of a benzazole according to any of claims 21 to 24 for the treatment or prevention of disorders associated with the abnormal expression or activity of JNK.
26. A method for inhibiting the expression and/or the activity of JNK
comprising the step of contacting cells expressing JNK with at least one benzazole derivative according to any of the claims 1 to 17.
comprising the step of contacting cells expressing JNK with at least one benzazole derivative according to any of the claims 1 to 17.
27. A method for the treatment of disease states mediated by JNK, comprising the administration to the patient a pharmaceutically active amount of a benzazole derivative according to any of the claims 1 to 17.
28. A pharmaceutical composition containing at least one benzazole derivative according to any of the claims 1 to 17 and a pharmaceutically acceptable carrier, diluent or excipient thereof.
29. Process for the preparation of a benzazole derivative according to any of claims 1 to 17, wherein the following reaction is performed:
whereby X and G are as above described and Y, Y' are suitable leaving groups like halogen.
whereby X and G are as above described and Y, Y' are suitable leaving groups like halogen.
30. Process according to claim 29, wherein the following reactions are performed with R1, R2, Y and X being as described above.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99811207.2 | 1999-12-24 | ||
| EP99811207A EP1110957A1 (en) | 1999-12-24 | 1999-12-24 | Benzazole derivatives and their use as JNK modulators |
| PCT/EP2000/013006 WO2001047920A1 (en) | 1999-12-24 | 2000-12-20 | Benzazole derivatives and their use as jnk modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2394809A1 true CA2394809A1 (en) | 2001-07-05 |
| CA2394809C CA2394809C (en) | 2011-03-15 |
Family
ID=8243214
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| CA2394809A Expired - Lifetime CA2394809C (en) | 1999-12-24 | 2000-12-20 | Benzazole derivatives and their use as jnk modulators |
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